Sodium Iodide → HCID 58160391, compound

HRID 588331Notes

Reaction equation

HRID 588331 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:11][CH:10]([CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[C:9]1=[O:38])=O)(C)(C)C.[I-:39].[Na+]>C(#N)C>[C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:19][C:14]([CH2:13][C@H:12]2[NH:8][C:9](=[O:38])[CH:10]([CH2:26][I:39])[CH2:11]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 58160410HCID 58160410, compound

Product 1

HCID 58160391HCID 58160391, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

122 mg (3R/S,5S)-5-Biphenyl-4-ylmethyl-2-oxo-3-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (11-a, R1=Boc, R4=Tosyl) prepared according to Example 49, Method 2 is added to acetonitrile (3 ml). Sodium iodide (105 mg) is then added to the mixture. The resulting mixture is heated at reflux overnight. The mixture is then concentrated under reduced pressure. Purification by column chromatography, eluting with ethyl acetate-heptane (1:1) gives (3R/S,5S)-5-biphenyl-4-ylmethyl-3-iodomethyl-pyrrolidin-2-one (12-a, R1=H, R5=I). 1H NMR (CDCl3): 2.13 (2H), 2.69 (2H), 2.82 (1H), 3.28 (1H), 3.35 (1H), 3.85 (1H), 5.84 (1H), 7.17 (2H), 7.28 (1H), 7.37 (2H), 7.49 (4H).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture is then concentrated under reduced pressure
  4. customPurification by column chromatography
  5. washeluting with ethyl acetate-heptane (1:1)

Sources & evidence

ORD record
ord-9c29d07b2485414b8afa459bd4e08b21
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Reaction notes

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